Abstract
We present results on reversible light-induced solubility of disperse red 1 (DR1) dye in a hydroxypropyl cellulose (HPC) matrix. The samples were prepared by dissolution of both DR1 and HPC in acetone and left to dry overnight in air to form not totally uniform red coatings. It is observed that both heating and illumination of the samples with visible light promote the appearance of a dark red coloration inside the heated or illuminated regions. This new phenomenon is attributed to a dissolution of dye and/or disruption of DR1 aggregates. It is confirmed by visible light and FTIR spectroscopies. UV–Vis spectra evidence disappearance of a band at 400 nm, which is attributed to DR1 aggregates, upon illumination of the samples with visible light. FTIR spectra show new bands at 1600, 1508, and 1342 cm−1 that were assigned to symmetric and asymmetric stretching modes of NO2 of the dissolved DR1. Results evidence a dye solubilization process throughout repeated trans–cis isomery induced by visible light. This process is also a new feature of the light induced molecular movements of azo-dyes and may be used in future for the photo-command of polymer properties and/or light storage. This work opens new perspectives to use natural polymers and composites in photonic applications. It also reveals the strong potential of azo-materials as light powered molecular motors.
Similar content being viewed by others
References
Apostoluk A, Chapron D, Gadret G, Sahraoui B, Nunzi J-M, Fiorini-Debuisschert C, Raimond P (2002) Quasi-phase-matched gratings printed by all-optical poling in polymer films. Opt Lett 27:2028–2030. https://doi.org/10.1364/OL.27.002028
Assis LMN, Sabadini RC, Santos LP, Kanicki J, Łapkowski M, Pawlicka A (2015) Electrochromic device with Prussian blue and HPC-based electrolyte. Electrochim Acta 182:878–883. https://doi.org/10.1016/j.electacta.2015.09.133
Barille R, Ahmadi-Kandjani S, Ortyl E, Kucharski S, Nunzi J-M (2006) Cognitive ability experiment with photosensitive organic molecular thin films. Phys Rev Lett 97:048701. https://doi.org/10.1103/PhysRevLett.97.048701
Böhm N, Materny A, Kiefer W, Steins H, Müller MM, Schottner G (1996) Spectroscopic investigation of the thermal cis-trans isomerization of disperse red 1 in hybrid polymers. Macromolecules 29:2599–2604. https://doi.org/10.1021/ma951238o
Cavallaro G, Donato DI, Lazzara G, Milioto S (2011) Films of halloysite nanotubes sandwiched between two layers of biopolymer: from the morphology to the dielectric, thermal, transparency, and wettability properties. J Phys Chem C 115:20491–20498. https://doi.org/10.1021/jp207261r
Choe DH, Jo GJ, Cha YG (2000) Optically induced anisotropy in photoresponsive sol-gel matrix bearing a silylated disperse red 1. Bull Korean Chem Soc 21:1222–1226
Cinar M, Coruh A, Karabacak M (2011) FT-IR, UV–vis, 1 H and 13 C NMR spectra and the equilibrium structure of organic dye molecule disperse red 1 acrylate: a combined experimental and theoretical analysis. Spectrochim Acta Part A Mol Biomol Spectrosc 83:561–569. https://doi.org/10.1016/j.saa.2011.09.003
Cocoyer C et al (2006) Implementation of submicrometric periodic surface structures toward improvement of organic-solar-cell performances. Appl Phys Lett 88:133108. https://doi.org/10.1063/1.2188600
Cojocariu C, Rochon P (2004) Light-induced motions in azobenzene-containing polymers. Pure Appl Chem 76:1479–1497. https://doi.org/10.1351/pac200476071479
Czaplicki R, Krupka O, Essaidi Z, El-Ghayoury A, Kajzar F, Grote J, Sahraoui B (2007) Grating inscription in picosecond regime in thin films of functionalized DNA. Opt Express 15:15268–15273. https://doi.org/10.1364/OE.15.015268
Delysse S, Raimond P, Nunzi J-M (1997) Two-photon absorption in non-centrosymmetric dyes. Chem Phys 219:341–351. https://doi.org/10.1016/S0301-0104(97)00106-7
Dumont ML, Sekkat Z (1993) Dynamical study of photoinduced anisotropy and orientational relaxation of azo dyes in polymeric films: poling at room temperature. In: San Diego ‘92. SPIE, pp 188–199. https://doi.org/10.1117/12.139169
Dumont ML, Hosotte S, Froc G, Sekkat Z (1994) Orientational manipulation of chromophores through photoisomerization. In: Optics Quebec. SPIE, pp 2–13. https://doi.org/10.1117/12.166297
Hubert C, Fiorini-Debuisschert C, Rocha L, Raimond P, Nunzi J-M (2004) Emission properties of organic light-emitting diodes directly patterned using optically controlled nanostructuration means. In: Photonics Europe, 2004. International Society for Optics and Photonics, pp 441–448. doi:https://doi.org/10.1117/12.552118
Kirby R, Sabat RG, Nunzi J-M, Lebel O (2014) Disperse and disordered: a mexylaminotriazine-substituted azobenzene derivative with superior glass and surface relief grating formation. J Mater Chem C 2:841–847. https://doi.org/10.1039/C3TC32034K
Lagugné Labarthet F, Sourisseau C (1996) Raman study of the photoisomerization and angular reorientation of azobenzene molecules in a DR1-doped polymer matrix. J Raman Spectrosc 27:491–498. https://doi.org/10.1002/(SICI)1097-4555(199606)27:6%3C491::AID-JRS988%3E3.0.CO;2-G
Ledwon P, Andrade JR, Lapkowski M, Pawlicka A (2015) Hydroxypropyl cellulose-based gel electrolyte for electrochromic devices. Electrochim Acta 159:227–233. https://doi.org/10.1016/j.electacta.2015.01.168
Lefin P, Fiorini C, Nunzi J-M (1998) Anisotropy of the photo-induced translation diffusion of azobenzene dyes in polymer matrices. Pure Appl Opt: J Eur Opt Soc Part A 7:71
Marino I-G, Raschellà R, Lottici PP, Bersani D (2008) Chromophore aggregation and photoinduced dichroism in sol–gel films. J Non-Cryst Solids 354:688–692. https://doi.org/10.1016/j.jnoncrysol.2007.07.072
Mazaheri L, Sabat RG, Lebel O, Nunzi J-M (2016) Unraveling the nucleation and growth of spontaneous surface relief gratings. Opt Mater 62:378–391. https://doi.org/10.1016/j.optmat.2016.10.003
Oliveira ON, dos Santos DS, Balogh DT, Zucolotto V, Mendonça CR (2005) Optical storage and surface-relief gratings in azobenzene-containing nanostructured films. Adv Colloid Interface Sci 116:179–192. https://doi.org/10.1016/j.cis.2005.05.008
Prado HJ, Matulewicz MC (2014) Cationization of polysaccharides: a path to greener derivatives with many industrial applications. Eur Polym J 52:53–75. https://doi.org/10.1016/j.eurpolymj.2013.12.011
Priimagi A et al (2012) Halogen bonding versus hydrogen bonding in driving self-assembly and performance of light-responsive supramolecular polymers. Adv Funct Mater 22:2572–2579. https://doi.org/10.1002/adfm.201200135
Rinaudo M (2016) Physicochemical behaviour of semi-rigid biopolymers in aqueous medium. Food Hydrocoll. https://doi.org/10.1016/j.foodhyd.2016.09.015
Schoelch S, Vapaavuori J, Rollet F-G, Barrett CJ (2017) The orange side of disperse red 1: humidity-driven color switching in supramolecular azo-polymer materials based on reversible dye aggregation. Macromol Rapid Commun. https://doi.org/10.1002/marc.201600582
Sebti I, Ham-Pichavant F, Coma V (2002) Edible bioactive fatty acid-cellulosic derivative composites used in food-packaging applications. J Agric Food Chem 50:4290–4294. https://doi.org/10.1021/jf0115488
Sentein C, Fiorini C, Lorin A, Nunzi JM (1997) Molecular rectification in oriented polymer structures. Adv Mater 9:809–811. https://doi.org/10.1002/adma.19970091009
Shirota Y (2000) Organic materials for electronic and optoelectronic devices Basis of a presentation given at Materials Chemistry Discussion No. 2, 13–15 September 1999, University of Nottingham, UK. J Mater Chem 10:1–25. https://doi.org/10.1039/A908130E
Sigma-Aldrich-Merck (2017) Hydroxypropyl cellulose. Sigma-Alfrich-Merck. http://www.sigmaaldrich.com/catalog/product/aldrich/435007?lang=en®ion=US. Accessed 17 July 2017
Tanaka A et al (2017) Nasal drug absorption from powder formulations: the effect of three types of hydroxypropyl cellulose (HPC). Eur J Pharmaceut Sci 96:284–289. https://doi.org/10.1016/j.ejps.2016.09.028
Taunaumang H, Solyga M, Tija MO, Miniewicz A (2004) On the efficient mixed amplitude and phase grating recording in vacuum deposited disperse red 1. Thin Solid Films 461:316–324. https://doi.org/10.1016/j.tsf.2004.01.100
Teboul V, Saiddine M, Nunzi J-M (2009) Isomerization-induced dynamic heterogeneity in a glass former below and above T g. Phys Rev Lett 103:265701. https://doi.org/10.1103/PhysRevLett.103.265701
Teboul V, Saiddine M, Nunzi J-M, Accary J-B (2011) An isomerization-induced cage-breaking process in a molecular glass former below Tg. J Chem Phys 134:114517. https://doi.org/10.1063/1.3563548
Viswanathan N, Kim D, Tripathy S (1999) Surface relief structures on azo polymer films. J Mater Chem 9:1941–1955. https://doi.org/10.1039/A902424G
Wei S, Ma Y, Luo J, He X, Yue P, Guan Z, Yang M (2017) Hydroxypropylcellulose as matrix carrier for novel cage-like microparticles prepared by spray-freeze-drying technology. Carbohydr Polym 157:953–961. https://doi.org/10.1016/j.carbpol.2016.10.043
Zerriaa A, El Ganaoui M, Gerardin C, Tazibt A, Gabsi S (2016) Physical incorporation of particles in a porousmedia: a path to a smart wood*. Eur Phys J Appl Phys 74:24607. https://doi.org/10.1051/epjap/2015150458
Zilker SJ, Bieringer T, Haarer D, Stein RS, van Egmond JW, Kostromine SG (1998) Holographic data storage in amorphous polymers. Adv Mater 10:855–859. https://doi.org/10.1002/(SICI)1521-4095(199808)10:11<855::AID-ADMA855>3.0.CO;2-H
Acknowledgments
The authors are grateful to FAPESP (Grants Nos. 2016/13184-0 and 2014/17174-4) for financial support given for this research work and to Marcos Cardoso and Prof. Cleber Mendonça, from IFSC-Universidade de São Paulo, for laser lab facility. A. Pawlicka also thanks The Brazilian National Council for Scientific and Technological Development (CNPq) for research grant Produtividade em Pesquisa No. 305029/2013-4.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Pawlicka, A., Sabadini, R.C. & Nunzi, JM. Reversible light-induced solubility of disperse red 1 dye in a hydroxypropyl cellulose matrix. Cellulose 25, 2083–2090 (2018). https://doi.org/10.1007/s10570-018-1672-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10570-018-1672-z